011 Where the Obstacle Becomes the Advantage
The Most Mindset
In this episode of the Most Mindset podcast, Michael Most interviews Bill Gross, a seasoned expert in probate real estate. Bill shares his unique journey from aspiring attorney to successful real estate agent, emphasizing the importance of understanding the probate process. He discusses the challenges and opportunities within the probate niche, the significance of building relationships, and the role of data in generating leads. Bill also highlights the importance of effective communication and the value of being an expert in court confirmation sales. The conversation concludes with insights...
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010 Becoming the Trusted Advisor in a Noisy Market
The Most Mindset
In this episode of The Most Mindset, Michael sits down with longtime friend Chris Ryder, the first real estate agent guest on the podcast, to unpack what actually drives success in today’s market. They talk about how a real friendship, not transactional, became a powerful partnership; why buyers often choose lenders for the wrong reasons; and how agents and loan officers can win by being the trusted advisor who communicates, protects the deal, and puts people first. Chris also shares his unusual path from theology into real estate, how he built his business like an entrepreneur, and the hard...
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009 Building a Career With No Plan B
The Most Mindset
In this episode, Michael Most interviews Aaron Tennison, a seasoned professional in the mortgage industry. They discuss Aaron's journey from a nomadic childhood in Alaska to his experiences in the Navy, and how these shaped his entrepreneurial spirit. Aaron shares insights into the challenges of the mortgage business, the importance of building relationships, and the lessons learned from his career. He reflects on influential books that have impacted his life and discusses his current success in a broker platform, emphasizing the value of adaptability and perseverance in a fluctuating...
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008 Communication Is Your Superpower
The Most Mindset
In this episode of The Most Mindset, Michael sits down with longtime friend and veteran loan officer Chris Davis to unpack a 25-year journey through the mortgage world. From growing up in Napa’s wine country and backpacking the globe, to stumbling into tech sales and then landing in mortgage banking right as the “internet” was becoming a thing, Chris shares how communication, curiosity, and relationship skills shaped his career. Together they break down what it’s really like to move from big banks to IMBs to the broker model, the fears that come with those transitions, and the freedom...
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007 From Big Banks to Broker Freedom
The Most Mindset
In this episode of the Most Mindset, Michael interviews Bob Hilsby, who shares his journey from a young entrepreneur in New York to a successful mortgage broker in California. Bob discusses his early career, the transition to the mortgage industry, and the lessons learned from owning a brokerage during the financial collapse. He reflects on his experiences in big banks, the challenges faced, and the importance of independence in the brokerage model. Bob also emphasizes the role of AI in enhancing business relationships and shares insights on maintaining personal well-being to support...
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006 Networking is the Key to Sales Success
The Most Mindset
In this episode of The Most Mindset, Michael Most interviews Ian Olsen, exploring his journey from a rugby player to a successful figure in the mortgage industry. Ian shares insights on the importance of relationships, the correlation between sports and business, and the transition to the broker model. He emphasizes the significance of curiosity in networking and the lessons learned over 25 years in the industry, including the importance of focusing on strengths and finding inspiration in personal growth. 00:30 Introduction to Ian Olson and His Journey 03:08 From Rugby to Trading: A Unique...
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005 From Bartender to Mortgage Expert
The Most Mindset
In this episode of the Most Mindset podcast, Mike Yeates shares his journey from bartending to becoming a successful mortgage professional. He discusses the importance of work ethic, organizational skills, and building relationships in the industry. Mike reflects on his experiences transitioning between different business models, including independent mortgage banks and brokerages, and highlights the flexibility and options available in the broker model. He also shares humorous anecdotes and insights into the challenges of self-employment, the impact of technology on the mortgage industry, and...
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004 Reputation is the Cornerstone of Business Success
The Most Mindset
In today’s episode of The Most Mindset, host Michael Most talks with industry veteran David Jaffe about his journey from retail to becoming a top mortgage originator. David shares insights from more than three decades in the business—covering the mindset, habits, and lessons that helped him thrive through multiple market cycles. He discusses the books and mentors that shaped his growth, his transition from banks to the broker model, and how coaching helped him find balance and renewed passion for his work. Packed with wisdom, humor, and practical advice, this episode is a must-listen for...
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003 Navigating Today's Mortgage Landscape
The Most Mindset
In this episode of the Most Mindset, Michael Most interviews Kerry Ogata, who shares his unique journey into the mortgage industry, influenced by his wife and the COVID-19 pandemic. They discuss the importance of communication, the role of technology and AI in the industry, and the personal stories that make the work rewarding. Kerry emphasizes the need for adaptability in the evolving mortgage landscape and offers advice for newcomers, highlighting the significance of training and understanding client needs. The conversation also touches on the dynamics of working with family in the business...
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002 From Design Dreams to Mortgage Success
The Most Mindset
In this engaging conversation, Michael Most interviews Chris Pessy, exploring his journey from a design background to a successful career in the mortgage industry. They discuss the evolution of the industry, the importance of wellness and balance, and the role of AI in enhancing efficiency. Chris shares valuable insights on building authentic relationships, navigating market changes, and offers advice for newcomers in the field. The conversation highlights the significance of personal branding and the power of genuine connections in achieving success. 00:00 The Journey Begins: Chris Pessy's...
info_outlineIn this episode of The Most Mindset, Michael sits down with longtime friend and veteran loan officer Chris Davis to unpack a 25-year journey through the mortgage world. From growing up in Napa’s wine country and backpacking the globe, to stumbling into tech sales and then landing in mortgage banking right as the “internet” was becoming a thing, Chris shares how communication, curiosity, and relationship skills shaped his career.
Together they break down what it’s really like to move from big banks to IMBs to the broker model, the fears that come with those transitions, and the freedom on the other side. Chris talks about difficult clients, underwriting realities, staying calm when millions are on the line, and how mountain biking, family time, and perspective keep him grounded. It’s a real, relatable look at how to evolve, stay steady under pressure, and build a career you actually enjoy.
00:25 Introductions & Background
01:19 From Tech Sales to a New “Internet” Product
04:19 Backpacking the World & Early Career Detours
05:59 Wine, Marine Biology & Choosing a Different Path
07:36 The Power of Communication & Sales Skills
10:47 Big Bank Years & High-Rise Projects
16:27 More Products, More Guidelines, More Opportunity
21:02 Jumping to the Broker Model & Saying “Yes” More Often
25:52 Underwriting Reality Checks & Funny Client Moments
31:29 Becoming “Calm Chris” Through Perspective
39:34 Books That Shaped Chris & Final Thoughts
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